Hair shampoo



United States Patent HAIR SHAMPOO Solomon Epstein, Chicago, Charles F. Fuchs, Evanston, and Martel] M. Gladstone, Chicago, 111., assiguors, by mesne assignments, to Emulsol Chemical Corporation, Chicago, 111., a corporation of Illinois No Drawing. Application January 2, 1952, Serial No. 264,681

14 Claims. (Cl. 252-117) This invention relates to hair shampoos and is especially concerned with improvements in shampoos of the liquid to paste or cream type, particularly in the liquid type.

Liquid and cream type shampoos have heretofore been manufactured and marketed on a substantial scale. The detergents which have been used in such shampoos fall into the category of soaps, that is, water-soluble salts of higher molecular weight fatty acids such as lauric acid, oleic, stearic acid, and the like, and the so-called synthetic detergents of which many are known and used, and various mixtures of soaps and synthetic detergents. One of the problems encountered in the preparation of satisfactory hair shampoos of the type with which the present invention deals resides in the matter of producing properly opaque products of desired consistency. Various of the products heretofore suggested for this purpose, for example, sodium stearate and monostearin, have not proven altogether satisfactory since, among other things, they have resulted in lowering the sudsing capacity of the detergents present in the hair shampoos or have otherwise adversely affected the cleaning or foaming and other properties of the hair shampoos.

The present invention is predicated on the discovery that, in hair shampoos of the type and utilizing detergents of the character hereafter described, especially liquid shampoos, through the incorporation of small proportions of certain addition agents, hereafter described in detail, excellent opacifying is obtained without lowering or appreciable lowering of the sudsing properties of the hair shampoo.

The addition agents referred to above comprise esterarnides of hydroxy-alkyl primary amines with normally solid higher molecular weight fatty acids. In such products, which are readily prepared, for example, by condensing 1 mol of an hydroxy-alkyl primary amine with at least about 2 mols of a normally solid higher molecular weight fatty acid at about 160-180 degrees C. for several hours, there is both an ester and an amide linkage. Typical of such ester-amides is the stearic acid ester-amide of monoethanolamine, the utilization of which comprises a particularly preferred embodiment of the invention, and which may be represented by the formula Other illustrative examples of ester-amides which can be used in accordance with the present invention are the stearic acid ester-amide of monopropanolamine; the stearic acid ester-amide of isopropanolamine; the palmitic acid ester-amide of monoethanolamine; the palmitic acid amide of monoethanolamine esterified with stearic acid;

. the arachidic acid ester-amid of monoethanolamine; and

the stearic acid ester-amide of hydroxy-ethyl ethylenediamine. Other illustrative hydroxyalkyl primary amines, whose ester-amides with normally solid higher molecular weight fatty acids or mixtures of such acids, can be used in accordance with the present invention, are

monobutanolamine; 2-amino-1,3-propanediol; l-amino- 2,3-propanediol; hydroxy-ethyl diethylenetriamine; glycerolamine; 2-amino-2-methyl-1,3-propanediol, and the like.

The detergents which are utilized in accordance with the present invention are selected from the followinggroups. Mixtures of any two or more of any of the fol lowing detergents, with or without supplemental detergents, can also be utilized.

1. Water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms, and particularly of such detergents are the sulfates of higher ali phatic alcohols derived from coconut oil, palm kernel oil, or babassu oil, in the form of their sodium or other watersoluble salts. Such detergents are disclosed, for example, in U. S. Patents Nos. 1,968,793; 1,968,794; and 1,968,797.

2. Water-soluble salts of sulfuric acid esters of aliphatic polyhydric alocohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms and particularly from 10 to 14 carbon atoms. Typical examples of such detergents are the mono-sulfates of lauric acid (or coconut oil fatty acid) monoglyceride (sodium salt); monosulfate of the lauric acid ester of diethylene glycol (sodium salt); and mono-sulfate of the myristic acid ester of diglycerol (sodium salt). These detergents are disclosed in detail in Reissue Patent No. 20,636.

3. Water-soluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms and particularly where the alkyl chain contains predominantly 12 to 14 carbon atoms.

Typical examples of such compounds are the sodium salts of an alkylated benzene sulfonic acid wherein the alkyl group contains approximately 12 carbon atoms and is derived from an olefin polymer such as a propylene tetramer or is derived from a kerosene fraction; the sodium salt of nonyl naphthalene sulfonic acid; and the sodium salt of dodecyl toluene sulfonic acid. Such detergents are disclosed in a large number of U. S. patents typical of which are the following: 1,992,160; 2,161,173;

0 izHzs C Hr-O Hr-O S O 3N8 OHi0 OHrCHrOSOsNB.

C12H25 CHCH2OSO3Na 5. Sulfated and sulfonated vegetable oils (including mixtures ofsuch sulfated and sulfonated oils). These are conventionally prepared from castor oil, olive oil, or oils containing glycerides of oleic acid by reaction with sulfuric acid or other sulfonating agents and then neutralizing. They are utilized in shampoos of the type which are, generally speaking, non-foaming, but they may be utilized in combination with detergents of the foaming type such as are described herein.

6. Condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1. Typical examples of such detergents are condensation products of 2 mols of diethanolamine with 1 mol of lauric acid or coconut oil mixed fatty acids; and condensation products of 2 mols of triethanolamine with 1 mol of lauric acid, myristic acid, or coconut oil mixed fatty acids. These detergents are particularly described in U. S. Patent No. 2,089,212.

7. Polyoxyalkylene glycol ethers of alkylatcd aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms and more particularly from about 10 to 14 carbon atoms. Such detergents are made, for example, by reacting an allcylated phenol or naphthol, in which the alkyl group contains from 8 to 18 carbon atoms, with an alkylene oxide, such as ethylene oxide or propylene oxide, particularly the former, to introduce several, usually from about 8 to about 20, oxyalkylcne groups. A typical example is an ethylene oxide derivative of p-tert-octyl phenol in which approximately 8 to 10 oxyalkylene groups are present.

8. Normally liquid soaps. These are commonly prepared in situ by saponifying a triglyceride oil, or mixture of oils, such as olive oil, palm oil, coconut oil, palm kernel oil, sesame oil, linseed oil, and the like, with caustic soda or caustic potash or mixtures thereof, and diluting to the desired concentration with distilled water. They are also commonly prepared by dissolving the desired quantity of a soft soap in a mixture of water and alcohol.

The detergent or mixture of detergents is utilized in variable proportions in the shampoo, depending upon the exact results desired and the particular nature of the formulation. In general, the detergent or mixture of detergents will fall within the range of about 8% to about 30% and, more particularly, in the range of about 15% to about 25%, by weight, of the shampoo. The ester-amide of the hydroxy-alkyl primary amine is utilized in minor proportions and, in most cases, the proportions thereof will fall within the range of about 1% to about or 6% with a good average in the range of about 2% to about 5%, based on the weight of the shampoo. In general, the water content of the shampoo will not fall substantially below 50% by weight of the shampoo. In the case of the paste or cream shampoos, a range of about 50 to about 65% of water and, in the case of liquid shampoos, a percentage in the range of 60 to 75% of water is satisfactory.

It is also advantageous, in various of the formulations, to utilize, in the shampoos, amides of isoprophanolamine with normally liquid higher molecular weight fatty acids. When utilized in the shampoo products of the present invention, the amount thereof employed will range up to about 6% and preferably will fall within the range of about 1 to 3% in most cases. Other supplemental ingredients can, of course, be incorporated into the shampoos for obtaining special effects, such as lanolin, sulfonated lanolin, perfumes, and the like.

The following examples are illustrative of shampoos made in accordance with the present invention. It will be understood that these examples are not intended to be restrictive since numerous other formulations can be made with different detergents, mixtures of detergents, and various proportions of the ingredients, with or without supplemental ingredients, all falling within the scope of the guiding principles and teachings set forth herein. All parts listed in said examples are by Weight.

Example 1 Lauryl sodium sulfate l0 Stearic acid ester-amide of monoethanolamine 2 Oleic acid amide of isopropanolamine 1.5 Water 32 Example 2 Dodecyl benzene sodium sulfonate l5 Stearic acid ester-amide of monoethanolamine 3 Oleic acid amide of isopropanolamine 2 Water 37 Example 3 Coconut oil fatty acid mixed monoand di-glyceridcs,

sulfated (Na salt) l2 Palmitic acid ester-amide of monoethanolamine 2 Oleic acid amide of isopropanolamine 1.2 Water 36 Example 4 Lauryl sodium sulfate 30 Dodecyl benzene sodium sulfonate l5 Stearic acid ester-amide of monoethanolaminc- 3 Water 52 Example 5 Condensation product of 2 mols diethanolamine and 1 mol lauric acid 12 Sulfonated castor oil 4 Stearic acid ester-amide of monoethanolamine 2 Oleic acid amide of isopropanolaminc 1.5 Water 42 Example 6 Polyoxyethylene glycol ether of alkylated phenol (e. g. Triton X-lOO or Antarox A200 or Antarox A-400) .W 10 Stearic acid ester-amide of monoethanolamin 2 Oleic acid amide of isopropanolamine 1 Water 24 Example 7 Condensation product of 2 mols diethanolamine and 1 mol lauric acid 7.2 Sulfosuccinic acid ester of myristic acid amide of monoethanolamine (Na salt) n 28.3 Lauryl sodium sulfate 9 Stearic acid ester-amide of monoethanolamine 3 Water 5 2.

Example 8 Mono-sulfate of coconut oil mixed fatty acid monoglycerides (Na salt) l6 Stearic acid ester-amide of monocthanolamine 5 Oleic acid amide of isopropunolamine 2 Water 27 In the preparation of the shampoos, the mixture of the ingredients is heated to about degrees C. with agitation until the mixture is homogeneous. Ft bile continuing the agitation, the mixture is cooled to about 30 to 35 degrees C. The perfume, if such is utilized, is added to the cooled mixture, with agitation, to effect distribution of said perfume.

What is claimed as new and desired to be protected by United States Letters Patent is:

1. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (l) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 cararcane bon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular, weight alkyl radical contains from 8 to 22 carbon atoms; sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid water-soluble soaps; said detergent comprising from about 8% to about 30%, by weight, of said shampoo; from about 1% to about 6%, by weight of said shampoo, of an ester-amide of an hydroxy-alkyl primary amine with a normally solid higher molecular weight fatty acid; and water, the water being present in amounts not substantially below 50%, by weight, of said shampoo.

2. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbonatoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid watersoluble soaps; said detergent comprising from about 8% to about 30%, by weight, of said shampoo; from about 1% to about 6%, by weight of said shampoo, of an ester-amide of an hydroXy-alkyl primary amine with a normally solid higher molecular Weight fatty acid comprising mainly stearic acid; and water, the water being present in amounts not substantially below 50%, by weight, of said shampoo.

3. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (l) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxylkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquidwater-soluble soaps; said detergent comprising from about 8% to about 30%, by weight, of said shampoo; from about 1% to about 6%, by weight of said shampoo, of an esteramide of monoethanolamine with a normally solid higher molecular weight fatty acid; and water, the water being present in amounts not substantially below 50%, by weight, of said shampoo.

4. An improved shampoo, having aliquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherei the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroXy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid water-soluble soaps; said detergent comprising from about 8% to about 30%, by weight, of said shampoo; from about 1% to about 6%, by weight of said shampoo, of a stearic acid ester-amide of monoethanolamine; and water, the water being present in amounts not substantially below 50%, by weight, of said shampoo.

5. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing front 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to l; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid water-soluble soaps; said detergent comprising from about 8% to about 30%, by weight, of said shampoo; from about 1% to about 6%, by weight of said shampoo, of an ester-amide of an hydroXy-alkyl primary mono-amine with a normally solid higher molecular weight fatty acid; and water, the water being present in amounts not substantially below 50%, by weight, of said shampoo.

6. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular Weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal" ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid water-soluble soaps; said detergent comprising from about 15% to about 25%, by Weight, of said shampoo; from about 2% to about by weight of said shampoo, of an ester-amide of an hydroxy-alkyl primary mono-amine with a normally solid higher molecular weight fatty acid; and water, the water being present in amounts of at least about 60%, by weight, of said shampoo.

7. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sult'onated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the bydroxy-alkyl amine to the fatty acid is not substantially less than 2 to 1; (7) polyoxyalkylene glycol ethers of alkylated aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid watersoluble soaps; said detergent comprising from about to about by weight, of said shampoo; from about 1% to about 5%, by weight of said shampoo, of an ester-amide of monoethanolamine with a normally solid higher molecular weight fatty acid; and water, the water being present in amounts of at least about 60%, by weight, of said shampoo.

8. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) Water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incompletely esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulfonic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfonated castor oil; (6) condensation products of hydroxy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to l; (7) polyoxyalkylene glycol ethers of alkylatcd aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid water-soluble soaps; said detergent comprising from about 15% to about 25%, by weight, of said shampoo; from about 1% to about 5%, by Weight of said shampoo, of an ester-amide of an hydroxy-alkyl primary mono-amine with a normally solid higher molecular weight fatty acid comprising stearic acid; and water, the water being present in amounts of at least about by weight, of said shampoo.

9. An improved shampoo, having a liquid to paste consistency, comprising essentially a mixture of at least one detergent selected from the group consisting of: (1) water-soluble salts of sulfuric acid esters of aliphatic alcohols containing from 8 to 18 carbon atoms; (2) water-soluble salts of sulfuric acid esters of aliphatic polyhydric alcohols incomplete.y esterified with fatty acids containing from 8 to 22 carbon atoms; (3) watersoluble salts of alkylated aromatic sulionic acids wherein the alkyl group contains a chain of from 8 to 22 carbon atoms; (4) water-soluble salts of higher molecular weight alkylated aromatic hydroxy-alkyl sulfuric acid esters wherein the higher molecular weight alkyl radical contains from 8 to 22 carbon atoms; (5) sulfcnated castor oil; (6) condensation products of hydroXy-alkyl amines with fatty acids containing from 8 to 18 carbon atoms and wherein the molal ratio of the hydroxy-alkyl amine to the fatty acid is not substantially less than 2 to l; (7) polyoxyalkylene glycol ethers of alkyiatcd aromatic compounds in which the nuclear alkyl group contains from 8 to 18 carbon atoms; and (8) liquid Water-soluble soaps; said detergent comprising from about 15% to about 25%, by weight, of said shampoo; from about 1% to about 5%, by weight of said shampoo, of a stearic acid ester-amide of monoethanolamine; and water, the water being present in amounts of at least about 60%, by weight, of said shampoo.

10. A shampoo in accordance with claim 1, containing up to about 6%, by weight, of the oleic acid amide of isopropanolamine.

11. A shampoo in accordance with claim 4, containing up to about 6%, by weight, of the oleic acid amide of isopropanolamine.

12. A shampoo in accordance with claim 5, containing up to about 6%, by Weight, of the oleic acid amide of isopropanolamine.

13. A shampoo in accordance with claim 6, containing up to about 6%, by weight, of the oleic acid amide of isopropanolamine.

14. A shampoo in accordance with claim 9, containing up to about 6%, by weight, of the oleic acid amide of isopropanolamine.

References Cited in the file of this patent UNITED STATES PATENTS 2,173,058 Kritchevsky Sept. 12, 1939 2,383,737 Richardson Aug. 28, 1945 2,383,738 Richardson Aug. 28, 1945 2,483,253 Young Sept. 27, 1949 2,490,459 Lilienfeld Dec. 6, 1949 2,519,062 Miskel Aug. 15, 1950 2,527,076 Preston Oct. 24, 1950 

1. AN IMPROVED SHAMPOO, HAVING A LIQUID TO PASTE CONSISTENCY, COMPRISING ESSENTIALLY A MIXTURE OF AT LEAST ONE DETERGENT SELECTED FROM THE GROUP CONSISTING OF: (1) WATER-SOLUBLE SALTS OF SULFURIC ACID ESTERS OF ALIPHATIC ALCOHOLS CONTAINING FROM 8 TO 18 CARBON ATOMS; (2) WATER-SOLUBLE SALTS OF SULFURIC ACID ESTERS OF ALIPHATIC POLYHYDRIC ALCOHOLS INCOMPLETELY ESTERIFIED WITH FATTY ACIDS CONTAINING FROM 8 TO 22 CARBON ATOMS; (3) WATERSOLUBLE SALTS OF ALKYLATED AROMATIC SULFONIC ACIDS WHEREIN THE ALKYL GROUP CONTAINS A CHAIN OF FROM 8 TO 22 CARBON ATOMS; (4) WATER-SOLUBLE SALTS OF HIGHER MOLECULAR WEIGHT ALKYLATED AROMATIC HYDROXY-ALKYL SULFURIC ACID ESTERS WHEREIN THE HIGHER MOLECULAR WEIGHT ALKYL RADICAL CONTAINS FROM 8 TO 22 CARBON ATOMS; (5) SULFONATED CASTOR OIL; (6) CONDENSATION PRODUCTS OF HYDROXY-ALKYL AMINES WITH FATTY ACIDS CONTAINING FROM 8 TO 18 CARBON ATOMS AND WHEREIN THE MOLAR RATIO OF THE HYDROXY-ALKYL AMINE TO THE FATTY ACID IS NOT SUBSTANTIALLY LESS THAN 2 TO 1; (7) POLYOXYALKYLENE GLYCOL ETHERS OF ALKYLATED AROMATIC COMPOUNDS IN WHICH THE NUCLEAR ALKYL GROUP CONTAINS FROM 8 TO 18 CARBON ATOMS; AND (8) LIQUID WATER-SOLUBLE SOAPS; SAID DETERGENT COMPRISING FROM ABOUT 8% TO ABOUT 30%, BY WEIGHT, OF SAID SHAMPOO; FROM ABOUT 1% TO ABOUT 6%, BY WEIGHT OF SAID SHAMPOO, OF AN ESTER-AMIDE OF AN HYDROXY-ALKYL PRIMARY AMINE WITH A NORMALLY SOLID HIGHER MOLECULAR WEIGHT FATTY ACID; AND WATER, THE WATER BEING PRESENT IN AMOUNTS NOT SUBSTANTIALLY BELOW 50%, BY WEIGHT, OF SAID SHAMPOO. 